Signs I may need to update my pop culture references

I consider myself reasonably current in the pop culture world. I’ve never seen an episode of The Hills, but I know about the infighting between Lauren and Spencer and whatsherface. I’ve only ever seen part of a season of American Idol, back when Fantasia won, but I bet I can name every winner. (I can’t say the same of Canadian Idol, but I refuse to accept that means I’m out of touch in any way.) I know John Mayer is a man-whore and Nicole Richie has cleaned up her act post-baby. I’m hip. I’m happening.

Yes, I realize the fact that I use the word hip means I’m totally not hip. But I’ve smacked into a few examples lately that made me confront just how unhip I might be.

But how else do you say it concisely?
I recently told a couple of people an anecdote that ended with the revelation that a friend had been “gaslighting me.” One knew what I meant by the phrase because he’d seen the movie, but the other had to use Wiktionary to figure out what the hell I was talking about (“To manipulate someone psychologically such that they question their own sanity”). In my defense, this is a reference that way predates my birth, to 1944’s Gaslight starring Ingrid Bergman. Wait, is that actually a defense? Whatever. It’s a great movie, a great concept, a great word, but I fear I need to stop using it as if people know what I mean. I probably won’t though, since I love it so much.

The pinnacle of beauty
I was trying to make an analogy about something and reaching for a comparison with the perfect example of perfect beauty, so I went to my long-time go-to example, Michelle Pfeiffer. Now, I will spit on you, virtually speaking, if you try to tell me she’s not one of the most beautiful people in the world -- and forget any qualifiers about age. But the woman hasn’t been making a lot of movies lately, having retreated to some beautiful Northern California ranch with her beautiful family or something, and doesn’t appear much on the cover of magazines or tabloids. She’s not exactly a current reference, is what I’m saying, not that her beauty isn’t current. I can’t make myself use obvious example Angelina Jolie, who is undeniably gorgeous but scares the crap out of me. That does not coincide with my image of beauty.

Was it that long ago?
A very white 20-something coworker was briefly wearing his hoodie with the hood up in the office the other day, so another coworker commented on the oddly casual look for our not-quite-that-casual office.
20-something: I’m going for the gangsta look.
Me: You look more like the Unabomber.
20-something: [blank stare]

Decisions, decisions. Do I make the effort to update my pop culture references, or do I accept the fact that people might not have a clue what I'm talking about? I'm leaning toward the latter -- after all, the outdated references are only the tip of the "what the hell is she talking about" iceberg anyway.